A historic downtown street at dusk with vintage street lamps, brick buildings, and a sign for 'FELSH POINT'.

Holiday Homes in Maryland

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Top Cities in Maryland

A street with red brick buildings, a white house with a red roof, and an American flag.
Holiday HomesHoliday Homes

Frederick

Frederick

Our top choices for Maryland holiday homes

A deck with green chairs and a fire pit, surrounded by a house and trees.

1. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (32 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is AU$712
includes taxes & fees
18 Oct - 19 Oct
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A beach with chairs and a pier in the background.

2. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AU$756
includes taxes & fees
19 Oct - 20 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A dining area with a rectangular table surrounded by white chairs, a chandelier above, and a television on the wall.

3. 3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Silver Spring
9.8 out of 10, Exceptional, (91 reviews)
"Large and great location"
United States
JoAnn J.
3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
A single-story brick house with a front porch, a garage, and a driveway.

4. Private Suite 3 near National Harbor Pvt Entry

Private Suite 3 near National Harbor Pvt Entry
Fort Washington
Private Suite 3 near National Harbor Pvt Entry
A rooftop terrace with a fire pit and seating area, overlooking a cityscape at night.

5. Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.6 out of 10, Excellent, (73 reviews)
"Great location within walking distance to so many places to eat and relax. Historic setting. Loved the brick wall’s throughout. Plenty of fans and ac to keep it cool even in the 101 degree temps."
United States
Clarence and Lisa B.
The price is AU$390
includes taxes & fees
20 Oct - 21 Oct
Rooftop Deck Escape! Free Parking!
A room with a fireplace, a mirror, a wreath, and a potted plant.

6. Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Historic District
9.4 out of 10, Exceptional, (22 reviews)
"Good location convenient to old town Annapolis and even can walk there"
United States
Thomas B.
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
A waterfront restaurant with tables and an umbrella, a dock with a boat, and a sign indicating emergency exit only.

7. Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape

Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape
Marley
9.4 out of 10, Exceptional, (10 reviews)
"Victor and Rose are fantastic hosts! We’ve booked with them multiple times and their property is just perfect for our group."
United States
MacKendrie P.
The price is AU$405
includes taxes & fees
15 Nov - 16 Nov
Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape
A bathroom with a towel rack, a mirror, a sink, and a potted plant.

8. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (8 reviews)
The price is AU$324
includes taxes & fees
19 Oct - 20 Oct
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A spacious kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

9. Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Downtown Ocean City
10.0 out of 10, Exceptional, (35 reviews)
"Great vacation area and accommodation!"
United States
Letizia
The price is AU$440
includes taxes & fees
1 Nov - 2 Nov
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
A living room with a sofa, a wooden coffee table, a red chair, a white cabinet with glass doors, and a chandelier.

10. Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (70 reviews)
"Centrally located, this little dollhouse is perfect for a couple or small family. Easily in walking distance to all important locations in St Michael’s. The A/C works great too!"
United States
Bonnie T.
Dollhouse in Central Historic St Michaels
A house with beige siding, a white door, and a window with a white frame.

11. Cozy 1BR with Full Bath & Your Own Entrance, and convenient parking

Cozy 1BR with Full Bath & Your Own Entrance, and convenient parking
Silver Spring
9.4 out of 10, Exceptional, (9 reviews)
"Great spot. Great stay."
United States
Bernard
Cozy 1BR with Full Bath & Your Own Entrance, and convenient parking
A garden with a variety of flowers and plants, a wooden structure, and a white fence.

12. Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Cumberland
9.8 out of 10, Exceptional, (53 reviews)
"Great stay"
United States
Michael R.
The price is AU$281
includes taxes & fees
28 Oct - 29 Oct
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A living room with a sofa, armchair, coffee table, dining table, chairs, and framed artwork on the wall.

13. Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Crofton
9.8 out of 10, Exceptional, (123 reviews)
"We really enjoyed our stay! Everything was clean and the parking was great. Location was perfect for all of our local travel plans."
United States
Kenneth A.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
A dining area with a table and chairs, three bay windows, and a vase with flowers.

14. Beautiful, Spacious Historic Victorian Near Ski Liberty

Beautiful, Spacious Historic Victorian Near Ski Liberty
Cascade
9.8 out of 10, Exceptional, (84 reviews)
"This is a beautiful home on a fantastic piece of land in rural northern Maryland. I highly recommend any group to stay here as a great mountain getaway."
United States
Max O.
Beautiful, Spacious Historic Victorian Near Ski Liberty
A modern kitchen with grey cabinets, a central island, and pendant lighting.

15. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is AU$494
includes taxes & fees
19 Oct - 20 Oct
Luxury Condo In Downtown Frederick
A large house with a swimming pool, deck chairs, and a covered patio area.

16. Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier
Cambridge
9.6 out of 10, Exceptional, (98 reviews)
"The host, Virgina, was amazing, so accommodating. Beautiful property. Looking forward to hopefully booking next year. "
United States
Susan B.
Private 2 Acre Waterfront Family Retreat with Pool & Pier
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

17. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (27 reviews)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
The price is AU$304
includes taxes & fees
19 Oct - 20 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A spacious living room with a sofa, a round coffee table, and a fireplace. There is a balcony with a view of the beach.

18. Luxurious 6bd Semi-Private Pool Steps to Beach Bikes Grill

Luxurious 6bd Semi-Private Pool Steps to Beach Bikes Grill
North Ocean City
8.8 out of 10, Excellent, (16 reviews)
"Liked the nearby beach and convenience"
United States
Arafat J.
Luxurious 6bd Semi-Private Pool Steps to Beach Bikes Grill
A modern kitchen with white cabinetry, a stainless steel refrigerator, wooden shelves, and pendant lighting.

19. Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cape Saint Claire
9.8 out of 10, Exceptional, (56 reviews)
"Place was awesome and Erin, the property manager, was so kind"
United Kingdom
Carter S.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
A hot tub with a view of a lake and a metal fence.

20. Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay
Perryville
9.2 out of 10, Wonderful, (65 reviews)
"Excellent location with beautiful sunrises and water views!"
United States
Kirk B.
Sailor's Sunrise Cottage - Chesapeake Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Maryland Hotel Reviews

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"Grand terrace restaurant was a complete disaster. Wait time was incredibly long for a waitress. After 15 minutes arrived at table took my order never returned with drinks. Meanwhile watched her serve coffee to a table that walked in right before us and even refilled there coffees. Us and another man both left without food. Restaurant was horribly understaffed. I would strongly suggest going to another establishment in area. Plenty of choices"
ANTHONY 3-night trip
Posted 2 hours ago
Grand Hotel Ocean City Oceanfront

Find out more about Maryland

Maryland Holiday Homes information

Number of reviews
860
Accommodation
4757 Holiday Homes
Lowest Price
AU$281
Highest Price
AU$756

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